John Massie Winston Jr. of Nags Head, Dec. 5

By on December 6, 2018

John Massie Winston, Jr., 73, of Nags Head, passed away on December 5, 2018. He was the son of the late John Massie Winston, Sr. and Virginia Ramsey Winston and was preceded in death by his sister, Mary Margaret Winston Pockrass.

John was a graduate of Patrick Henry High School and Randolph-Macon College and earned a Master’s Degree from the University of Virginia. He enjoyed spending time on and near the water in his boat and at the Outer Banks.

John had a distinguished career of 48 years in public education, serving for 32 years in Spotsylvania County Public Schools in Fredericksburg, VA and for 16 years in Dare County Schools in Nags Head, NC.

He began as a 7th grade math teacher at John J. Wright Middle School in 1968. After four years, he became a visiting teacher for the school district before being assigned as acting principal at Livingston Elementary School. He served as principal for a total of 27 years, including stints at Chancellor Elementary, Spotswood Elementary, Battlefield Middle School, and as the principal who opened Chancellor High School in 1988.

In 1995, he was tapped to become the Director of Secondary Instruction. In 1997, he was promoted to Assistant Superintendent for Personnel, a post he held until he retired from Virginia Public Schools in 2000.

Later that year he became the Assistant Superintendent of Dare County Schools, where he worked for 16 years before retiring from North Carolina Public Schools.

Those fortunate enough to work with him described him as always remaining calm and giving good advice, all the while maintaining a quick, but wry sense of humor.

John is survived by his wife of 51 years, Karen C. Winston; sons, Andrew Winston and Patrick Winston and brother, Carey Winston (Faye).

The family will receive friends on Friday, December 7, 2018 from 5-7pm at Nelsen Funeral Home & Crematory – Reid Chapel, 412 S. Washington Highway, Ashland, VA 23005, where a funeral service will take place on Saturday, December 8, 2018 at 1pm. Interment will follow in Woodland Cemetery, Ashland, VA.

In lieu of flowers, memorial contributions may be made to Dare County EMS or Feline Hope Animal Shelter, 843 Herbert Perry Rd, Kitty Hawk, NC, 27949.

Online condolences may be registered at

Recent posts in this category

Recent posts in this category
  • Nancy T. Besterci of Kitty Hawk, May 18

    Nancy was raised in Alexandria, VA, where she worked and met her husband Mark. The two recently realized their dream of retiring to the Outer Banks in February of 2019. Nancy loved the beach and watching the rain fall.

  • Robert “Bob” Powers Hockenberry of KDH, May 15

    Bob completed his high school studies and enlisted in the U.S. Navy, where he served honorably for several years. Bob then graduated from college in Denver, CO and quickly gained employment in electronics as a skilled technician.

  • Barry Lynn Statler of Manteo, May 13

    Barry Lynn Statler, 64, died suddenly at his Manteo home May 13, 2019. He was born in Chambersburg, PA and lost his wife several years ago. Barry was a skilled contractor for many years despite a leg disability he had since childhood.

John was a fine gentleman and educator of the highest order. I worked with him for 8 years while I served on our Board of Education. He was the best listener I’ve ever met. A room filled with debate would fall silent in order for those present to hear his comments whenever he spoke. Our school district was so fortunate to have a man of his caliber serving our students and families. He is and will be missed. I offer our heartfelt condolences to Mrs. Karen Winston, his wife, and their family.